Process for the production of new derivatives of the hydantoin.



UNITED STATES PATENT OFFICE.

LEO HERMANNS, OF HEIDELBERG, GERMANY, ASSIGNOR TO FARBWERKE VORM.

MEISTER LUCIUS & BR'ONING, OF HOCHST-ON-THE-MAIN, GERMANY, A CORPO-RATION OF GERMANY.

PROCESS FOR THE PRODUCTION OF NEW DERIVATIVES OF THE HYDANTOIN.

No Drawing,

T 0 all whom it may concern:

Be it known that I,Lr.o HERMANNS, Ph. D., chemist, a citizen of theEmpire of Germany, residing at Heidelberg, in the Empire of Germany andState of Baden, have invented certain new and useful Improvements inProcesses for the Production of New Derivatives of the Hydantoin, ofwhich the following is a specification. I

I have found that new -arylalkylhydantoins which are very valuable ashypnotics, are obtained by the action of hypohalogenites onarylalkylcyanacetamids. The transformation takes place in the sense ofthe following formula:

The new compounds are manufactured in the following manner:

Example: To a solution of 15.6 grams of phenylcyanacetamid (see Amem'c.0hem z'cal Journal, v0. 32, 20) in 250 cc. of absolute alcohol is addeda solution of 2.3 gr. of sodium in absolute alcohol. The sodium compoundthus formed is converted into the phenylethylcyanacetamid by adding 11gr. of ethylbromid and boiling on the water bath. After distilling offthe largest part of the alcohol, the phenylethylcyanacetamid isprecipitated by water (melting point 117 C.). It is easily soluble inhot diluted alcohol, difiicultly soluble in ether and benzone.

15 grams of phenylethylcyanacetamid are heated to boiling with 225 cc.of hypo bromite solution, prepared from 12.8 grams of bromin and acaustic soda lye of twentyfive per cent. strength. After cooling, somecc. of sulfurous acid are added, the whole is filtered, and thephenylethylhydantoin is precipitated by hydrochloric acid.Recrystallized from alcohol it constitutes a colorless compound which,melts at 198? 0., being readily soluble in acetone, alcohol and glacialacetic acid and insoluble in water and benzene; when combinedwithalkalis it forms salts which are readily soluble in water.

Specification of Letters Patent.

Application filed February 14, 1916. Serial No. 78,248.

In the present process the hypohalogenites I generally are equivalentsof sodium hypobromite, and may be used in substitution therefor.

Having now described my invention, what I claim is:

1. A process for producing arylalkylhydantoins of the formula:

which consists in treating arylalkylcyanacetamid with hypohalogenites.

' 2. A process for producing phenylethylhydantoin of the formula:

which consists in treating phenylethylcyanacetamid with sodiumhypohalogenite.

3. As new products, the arylalkylhydantoins of the formula:

a colorless compound melting at 198 C., insoluble in water, easilysoluble in hot acetone, alcohol and glacial acetic acid, forming withalkalis salts which are soluble in water.

In testimon whereof I afiix my signature in presence 0 two witnesses.

LEO HERMANNS.

Witnesses:

GUSTAV SCHILLING, C. Lumms BROWN.

